Chemoselective reactions of 3-benzyloxy-1,2-o-quinone with organometallic reagents.

Abstract

Chemoselective additions of organometallic reagents to 3-benzyloxy-1,2-o-quinone are described. Various nucleophiles are shown to undergo selective 1,2-addition, 1,4-addition, and etherification. Selective 1,2-additions provide stable, nondimerizing o-quinols as a novel alternative to oxidative dearomatization. 
DOI: 10.1021/ol9004068

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